ORGANIC CHEMISTRY

Hydrocarbons

Made from Hydrogen and Carbon

Alkenes

C-C saturated

C=C unsaturated

Alkenes

Ethene

CnH2n

Alkanes

Methane

CnH2n+2

Naming compounds depends on

Type of organic compound

If its an Alkane, the name ends in -ane

If an Alkene, it ends in an -ene

If an alcohol, it ends with anol

If a carboxylic acid, it ends with anoic acid

Depends on number of Carbons atoms present in the structure

If it has one carbon, the name starts with meth

2 carbons starts with, Eth

3 carbons starts with, prop

4 carbons start with, But

5 carbons start with, Pent

6 carbons starts with, Hex

7 carbons starts with, Hept

8 carbons start with, Oct

9 carbons start with, Non

10 carbons start with, Dec

Esthers

Formula CnH2n+2O

Properties

polar

usually soluble in water

melting/ boiling points less than alcohols

Subtopic

Esterfication

Esters are formed by the condensation reactions of a carboxylic acids and alcohol

Sweet and fruity smell

Flavourings, perfumes, solvents

C2H5OH+CH3COOH->CH3COOC2H5+H2O

First part: Alcohol Second part: Carboxylic acid

Alcohol+ Carboxylic Acid

Hydrolysis

reflux with acid/base

Acid

Reversible

CH3COOC2H5+H2O-><- CH3COOH+CH3CH2OH

Base

Not reversible

Alcohol+Sodium salt of COOH

CH3COOCH2CH3+NaOH->CH3COO-Na+CH3CH2OH

Soluble base,NaOH aq

IUPAC naming: to name a ester, it must be identified what the alcohol is. The ol and yl is added. For the carboxylic acid the -oic acid is dropped and replaced with -oate

Hybridization

subsitution of alcohols for halogen are an SN1 reactions. The easier it is to form, the faster the SN1 reaction will be

Sigma bonds

The bonds formed in methane between carbon and hydrogen atoms

formed by the head on overlap of two orbitals

Describing and comparing the physical properties of Aliphatic and Aromatic hydrocarbons ( including what reactions the hydrocarbons go through)

Halides

Can be added or subsituted onto hydrocarbons chains

Organic Halids

are polar, higher boiling point than corresponding hydrocarbon more soluble in polar solvents

Organic Alcohols

Can be created by hydration of alkenes and alkynes and others

Hydroxyl group

changes the properties of the hydrogen. Greater solublitity in water, higher melting/ boiling point

Hydration reactions ( addition ) Alkenes -> Alcohols can produce primary, secondary, and tertiary alcohols

Dehydration reactions ( elimination) reaction that involves the removal of H2O

undergoes complete combustion

Subsitiution of Alcohol for Halogen group

More stable carboncation, the more favourable and quicker reaction

Organic Ethers

polar molecules

slightly higher boiling point than alkanes, but much lower than alcohols

Soluble in polar and non polar solvents

Reactions with Ethers

condensation reaction ( dehydration)

Aldehydes and Ketones

Compared to alkanes, higher melting/ boiling point. And great solubility

Carboxylic acids

properties compared with alkane

high polar function ( H bond)

increase in melting/ boiling points, greater water solubility. produces H ions, acidic

Condensation reaction

Esters

Polar functional group, loses ability to form H+

Relative to the carboxylic acid, melting/boiling point decreases and less soluble in water

Amines

Increased solubility in polar solvents

Produces basic solution

Subsitution reaction

Amides

properties depend on the amount of H atoms bonded to N and chain length

Alcohols

Physical Properties

polar

soluble in water

very flammable

melting/boiling points higher than alkanes

reactions

combustion: alcohol + oxygen -> carbon dioxide and water

esterification: alcohol + carboxylic acid ->

esters can produced fro the condensation reaction of alcohols

can be produced by the hydration reaction of a alkene

can be reversed by dehydration reaction to produce a alkene and water

Polimerization: - addition-breaking of C=C bonds in smaller alkene compounds

Condensation- joining smaller molecules by elimination

Types of Alcohols

primary alcohols: hydroxyl group -OH is bonded to a carbon at the end of the chain

Secondary Alcohol: -OH is bonded to a carbon atom is attached to 2 other carbon atoms

Tertiary Alcohol: Hydroxyl group -OH is bonded to a carbon atom that has three alkyl groups, bonded to it

Ketones and Aledehydes

hydrocarbons containing C=O bonds, in the group chain

Reactions

Oxidation reactions: involves the addition of oxygen atoms or loss of hydrogen atoms

Properties

Carbonyl group is polar, but cannot hold H bonds

Lower boiling points and higher

Amines

Hydrocarbons with an amino acid, bonded to a carbon chain

increased soulublity, in polar solvents

produce basic solutions

Properties

higher bp than alkanes, but lower than alcohols and less soluble in water than reactive alcohols

Higher bp and more soluble in water than reactive hydrocarbons

Reactions

substitution: an organic halogen can react with ammonia to produce amine

Amides

Hydrocarbon chains with a terminal carboxyl group bonded to an amino group

Produces stable bonds

weak bases, more soulble in water

Reactions

Condensation reaction, a carboxylic acid can react with ammonia or a primary or secondary amine to produce an amide

Key to Carbons felxibility

Sp3 hybridization occurs when a C has 4 attached groupls

Sp3 hybrid orbital has 25% and 75% p character

each Sp3 hybrid orbital is involved in a sigma bond formation

Sp2 hybridization occurs when a c has 3 attached groups

each Sp2 hybrid orbital involved in a sigma bond formation and the remaining p orbitals from the pi bonds

Sp hybridization occurs when a C has 2 attached groups

The 2 sp hybrids are at 180 angle

Each Sp hybrid orbitals is involved in a sigma bond formation and the p orbitals forms tow pi bonds

a triple bond= sigma+ two pi bonds

Unsaturated Compounds

Alkenes: Have 1 double carbon somewhere in the chain

General formula: CnH2n

Molecular formula

CH2: Because of the structure is not stable

1 C2H4

Ethene

2 C3H6

Propene

3 C4H8

But-1-ene

4 C5H10

Pent-1-ene

5 C5H12

Hex-1-ene

6 C6H14

Hept-1-ene

7 C7H16

Oct-1-ene

8 C8H18

Non-1-ene

9 C9H20

Dec-1-ene

Saturated Compounds

Alkanes: Have single bonds between carbon atoms

CH4

Methane

C2H6

Ethane

C3H8

Propane

C4H10

Butane

C5H12

Pentane

C6H14

Hexane

C7H16

Heptane

C8H18

Octane

C9H20

Nonane

C10H22

Decane

Peperation

Forms Nitriles

Hydrolysis

Will dilute in HCL

Polar

High melting/boiling points

Reactions with alcohol-esterfication

General formula CnH2n+1COOH

Molecular Formula

1 HCOOH

Methanoic acid

CH3COOH

ethanoic acid

C2H5COOH

propanic acid

C3H7COOH

butanoic acid

C4H9COOH

pentanoic acid

C5H11COOh

hexanoic acid

Carbocylic acid

Ester

Amides

Aldehydes

Alcohol

Amine

Ketones

Ethers

electron geometry

Doulbe bonds have a trigonal planar geometry, with bonds angles to 120 and a flat shape

Atoms with five bonds create trigonal bipyramid geometry

3 atoms bond in the place of the central atom with 120 bond angles

the other 2 atoms are perpendicular an 2N2 addition reaction

methane is the smallest hydrocarbon

Carbons valence electron can hybridize in three different ways

Sp3- single bonds Sp2-double bonds sp triple bonds of carbon

methanes for identical hybrid sp3 are arranged in a tetrahedral to minimize electrostatic repulsion. Which creates sigma bonds

Pi bonds

Consists of two p orbitals that overlap above and below a sigma bond. A double bond has one sigma bond and one pi bond

more reactive than sigma bonds

Aromatic Compounds

Benzene

Structure

Carbon to carbon ring all are the same length

flat 6 carbon ring with a hydrogen atom bond to each carbon atom

Properties

insoluble in water

Higher melting/boiling points than alkynes

Alkenes

Formula CnH2n

higher melting/boiling points than alkanes

can undergo addition reaction

hydrogenation -> alcohols

other functional groups C=C

Unsaturated compounds

IUPAC name: -ene

Alphatic compunds

Alakanes

formula CnH2n+2

saturated hydrocarbon

insoluble in water

soluble in organic solvents

nonpolar

Saturated compounds that cannot undergo further addition reactions, only subsitution reaction

Cyclivc Alkane: Cyclohexane

Alkynes

Alkynes formula CnH2n-2

unsaturated hydrocarbons

consist of at least 2 carbons bonded together by a triple bond

non polar

insoluble in water

higher melting/boiling points than alkenes

hydrogenation

undergo reactions

Hydration- water reacts with alkyne and produces a organic compound with a hydroxyl group (-OH)

IUPAC name-yne